Trail Running Calendar near Waukesha 2026-2027

September 2027

Trail Run

Timed trail event at Richard Bong State Park on September 25, 2027, offering 3, 6 and 12 hour options on repeated 0.97 mile loops with hourly challenges.

October 2027

Oct

9

Sa

Ultratrax Alpine Valley

East Troy | 18 mi from Waukesha

Trail Run 7 mi 14 mi 21 mi 28 mi

Timed 10 hour trail event at Alpine Valley, Elkhorn WI with clearly marked single track loops of 7, 14, 21 and 28 miles and optional weighted divisions.

Oct

9-10

Sa - Su

Helios

Eagle | 15 mi from Waukesha

Trail Run

Timed 6, 12 and 20 hour trail ultraruns in Eagle Wisconsin with solo and relay options across three loop distances and manual lap timing.

Oct

16

Sa

Golden Kettle Trail Series - Scuppernong

North Prairie | 10 mi from Waukesha

Trail Run 3 mi 5 mi 11 mi 19 mi

Trail races at Scuppernong Trailhead in Kettle Moraine State Forest with 3.1, 5.4 and 10.8 mile loops plus a 19.3 mile combined option.

Oct

30

Sa

That's an Awful Idea 5K - Let's Do It

Oconomowoc | 15 mi from Waukesha

Trail Run 3 mi

A fall event in Oconomowoc with multiple running and ruck options, featuring 3.1 mile courses, a 0.5 mile hill race, and a free kids climb.

Oct

30

Sa

Among the Trees

Dousman | 12 mi from Waukesha

Trail Run 50 km 100 km

Trail ultramarathon on the Ice Age Trail offering 100k and 50k routes, wooden medal branding, aid stations, and fall foliage in the Southern Kettle Moraine Forest.